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Bill Flynn: How Leaders Doom Their Company

Episode 82

About Bill Flynn: Bill has more than 30 years of experience working for and advising hundreds of companies including startups, where he has a long record of success. He worked for 10 different high-tech startups in different market segments such as speech recognition, e-commerce, and affiliate marketing. He was a vice president of sales eight times, was twice a chief marketing officer, and once a general manager of a division of a $100 billion IT services company. He has had five successful outcomes with two IPOs and seven acquisitions, including a turnaround during the 2008 financial crisis. And then he pivoted to becoming a business growth coach.

Bill has multiple certifications as a growth coach. He has a certificate of distinction with the Founders of NeuroLeadership. He's a Certified Predictive Index partner, an author, and an international speaker. Bill's best-selling book, “Further, Faster: The Vital Few Steps That Take the Guesswork out of Growth” continues to have a five-star rating.


In this episode, Jordan and Bill discuss:

  • Why businesses fail.

  • The three key factors in business success

  • Why performance is a team sport

  • How to create an anti-fragile environment

  • Turning off your brain’s auto-pilot

Key Takeaways

  • Businesses fail because they make small mistakes in many areas creating a heavy burden on the leader and eventually sinking the business.

  • There are only 2 constituencies you should care about- Your customers and your team vs. focusing on beating your competition.

  • Teams get most of the work done in the company. Leaders must attract the right people, put them in the right teams, find a way to grow them, and provide an exit strategy when necessary.

  • Neuroleadership focuses on creating a more brain-friendly organization by making sure interactions in the workplace don’t put people’s brains in a threatened state.

  • Most of our decisions are made automatically without thinking. It takes a lot of work, time, and effort, but it is possible and it is worth it to slow down your bad habits and create better ones to replace them.

“[On creating psychological safety] It starts with you, you have to say, I'm a human being”. And that starts with three things: “I don't know”, “I'm sorry”, and “I need help”. When you can do that. you're giving permission for your team to be human beings. That generally raises the level of the team, productivity, and engagement.” — Bill Flynn

Connect with Bill Flynn:

Jordan Goldrich

Your host, Jordan Goldrich, grew up in a loud New York family and once lost an executive position because of his style. He is co-author of the Amazon Best Seller, Workplace Warrior®: People Skills For The No-Bulls**t Executive, Chief Operations Officer, Master Corporate Executive Coach, and Licensed Clinical Social Worker. His guests are part of his international network of Workplace Warrior® executives, master corporate executive coaches, and thought leaders. Each guest will engage you in conversation about their successes, mistakes, and solutions. You will get strategies for being completely authentic, while you fulfill your commitment to your organization, build positive relationships, and take performance to an even higher level.

Connect with Jordan Goldrich: 

For executives wanting a complimentary executive coaching conversation:



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